Thomas E. Storr
Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library
Storr, Thomas E.; Cully, Sarah J.; Rawling, Michael J.; Lewis, William; Hamza, Daniel; Jones, Geraint; Stockman, Robert A.
Authors
Sarah J. Cully
Michael J. Rawling
William Lewis
Daniel Hamza
Geraint Jones
Robert A. Stockman
Abstract
The application of a tandem condensation/cyclisation/[3+2]-cycloaddition/elimination reaction gives an sp3-rich tricyclic pyrazoline scaffold with two ethyl esters in a single step from a simple linear starting material. The successive hydrolysis and cyclisation (with Boc anhydride) of these 3-dimensional architectures, generates unprecedented 16-membered macrocyclic bisanhydrides (characterised by XRD). Selective amidations could then be achieved by ring opening with a primary amine followed by HATU-promoted amide coupling to yield an sp3-rich natural product-like library.
Citation
Storr, T. E., Cully, S. J., Rawling, M. J., Lewis, W., Hamza, D., Jones, G., & Stockman, R. A. (2015). Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library. Bioorganic and Medicinal Chemistry, 23(11), https://doi.org/10.1016/j.bmc.2014.12.050
Journal Article Type | Article |
---|---|
Acceptance Date | Dec 18, 2014 |
Online Publication Date | Dec 29, 2014 |
Publication Date | Jun 1, 2015 |
Deposit Date | Sep 28, 2017 |
Publicly Available Date | Mar 28, 2024 |
Journal | Bioorganic and Medicinal Chemistry |
Print ISSN | 0968-0896 |
Electronic ISSN | 1464-3391 |
Publisher | Elsevier |
Peer Reviewed | Peer Reviewed |
Volume | 23 |
Issue | 11 |
DOI | https://doi.org/10.1016/j.bmc.2014.12.050 |
Keywords | sp3-rich; Natural product-like; Scaffold; Cycloaddition; Two-directional; Macrocycle; Library; Tandem |
Public URL | https://nottingham-repository.worktribe.com/output/750700 |
Publisher URL | http://www.sciencedirect.com/science/article/pii/S0968089614009080 |
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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc-nd/4.0
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